Kid-friendly holiday rentals in Chester
Find and book unique kid-friendly rentals on Airbnb
Top-rated kid-friendly rentals in Chester
Guests agree: These kid-friendly rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chester kid-friendly rentals
Child-friendly house rentals
Home in Ludlow
4.92 out of 5 average rating, 139 reviews149 Upper Crossroad Unit A
6–13 Nov
Home in Winhall
4.99 out of 5 average rating, 349 reviewsStunning mid-century house on 2.5 private acres
1–8 May
Home in Grafton
4.92 out of 5 average rating, 186 reviewsRetro Modern Barn Apartment
2–9 Nov
Home in Weston
4.95 out of 5 average rating, 227 reviewsReillys Rest -GreenMtns! Secluded-Pet-Kid friendly
13–20 Sep
Home in Londonderry
4.97 out of 5 average rating, 117 reviewsWild Blossom Farmhouse - a lovely family getaway
13–20 May
Home in Grafton
4.97 out of 5 average rating, 130 reviewsEphriam Bruce House- ON RIVER IN VILLAGE CENTER
16–23 Sep
Home in Putney
4.95 out of 5 average rating, 308 reviewsCozy Train Depot in Putney Vermont
17–24 Oct
Home in Weston
4.86 out of 5 average rating, 106 reviews4 Bedroom Family Ski House w/ WiFi, cable!
2–9 Oct
Kid-Friendly apartment rentals
Apartment in Claremont
4.88 out of 5 average rating, 111 reviewsBeautiful 1 bedroom apartment with balcony
3–10 Jan
Apartment in Weston
4.86 out of 5 average rating, 129 reviewsCozy Guesthouse in Heart of VT
22–29 Aug
Apartment in Springfield
4.91 out of 5 average rating, 222 reviewsFarm Barn apt. 3 bedr, 2 bath, fiberoptic internet
10–17 May
Apartment in West Townshend
4.91 out of 5 average rating, 313 reviewsPrivate Apt on Farm, Magnificent views, Hot tub
6–13 May
Apartment in Manchester
4.99 out of 5 average rating, 148 reviewsPrivate two-bedroom suite within a two-story house
1–8 May
Apartment in Bellows Falls
4.95 out of 5 average rating, 182 reviewsVillage Flat with Antique Billiards
18–25 Mar
Apartment in Poultney
4.94 out of 5 average rating, 306 reviewsCozy Poultney Village Apartment
23–30 Jan
Apartment in Rutland
4.96 out of 5 average rating, 522 reviewsYour home away from home
27 Oct – 3 Nov
Child-Friendly Holiday Condos
Condo in Killington
4.95 out of 5 average rating, 130 reviews🎿Cozy Fireplace Condo-Mins. to Everything 🚵
5–12 Aug
Condo in Killington
4.81 out of 5 average rating, 140 reviews1BR Modern Condo @ Whiffletree Ground Fl Walkout
10–17 May
Condo in Brattleboro
4.92 out of 5 average rating, 284 reviewsPrivate & Quiet Studio Apt. in Vermont
15–22 Oct
Condo in Stratton
4.94 out of 5 average rating, 138 reviewsUpdated Ski in/Ski out Stratton Condo!
8–15 Jun
Condo in Ludlow
4.99 out of 5 average rating, 100 reviewsUpdated Main St Condo in downtown Ludlow!
31 Aug – 7 Sep
Condo in Killington
4.94 out of 5 average rating, 152 reviewsBright Ski on/off Condo Full Kitchen-Free Shuttle!
16–23 May
Condo in West Dover
4.94 out of 5 average rating, 181 reviewsComfy Condo - 2 Min Walk to Carinthia Grommet Lift
7–14 Nov
Condo in Killington
4.89 out of 5 average rating, 203 reviewsKillington-Pico ski in/out Studio at base of Pico
30 May – 6 Jun
Quick stats about holiday rentals that are kid-friendly in Chester
Total rentals
20 properties
Wi-Fi availability
20 properties include access to Wi-Fi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
550 reviews
Nightly prices starting at
$151 NZD before taxes and fees
Destinations to explore
- Cambridge Holiday rentals
- Burlington Holiday rentals
- Lake George Holiday rentals
- Lake Placid Holiday rentals
- Philadelphia Holiday rentals
- Jersey City Holiday rentals
- New York Holiday rentals
- The Hamptons Holiday rentals
- Boston Holiday rentals
- Montreal Holiday rentals
- Québec City Holiday rentals
- Québec Holiday rentals
- Kid-friendly rentals United States
- Kid-friendly rentals Boston
- Kid-friendly rentals Vermont
- Kid-friendly rentals Vermont
- Kid-friendly rentals New York
- Family-friendly rentals Chester
- Rentals with a fire pit Chester
- Pet-friendly rentals Chester
- Rentals with a fireplace Chester
- Rentals with outdoor seating Chester
- Monthly Rentals Chester
- Rentals with a washing machine and dryer Chester
- Rentals with a patio Chester
- House rentals Chester
- Kid-friendly rentals Windsor County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom